NPASS Compound

Structure

CID47059 OpenBabel06191715382D 24 27 0 0 1 0 0 0 0 0999 V2000 -5.3386 1.2999 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7885 4.0943 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7169 1.1334 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7877 2.2748 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7878 1.3649 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5759 -0.0002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3640 1.3645 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7879 -0.4550 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3641 2.2744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9400 1.3643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7882 2.2746 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4738 2.1720 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4737 1.4667 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.1519 0.9094 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0003 2.7296 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5761 0.9097 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7881 1.3647 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0001 0.9099 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9401 2.2742 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.7282 2.7291 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.1521 2.7293 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 -5.5479 2.3342 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0004 3.6395 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 2 24 1 0 0 0 0 4 5 2 0 0 0 0 4 15 1 0 0 0 0 5 18 1 0 0 0 0 6 8 2 0 0 0 0 6 16 1 0 0 0 0 7 9 1 0 0 0 0 8 21 1 0 0 0 0 9 22 1 0 0 0 0 10 14 1 0 0 0 0 10 19 1 0 0 0 0 11 15 2 0 0 0 0 11 17 1 0 0 0 0 12 13 1 0 0 0 0 12 22 1 0 0 0 0 13 3 1 6 0 0 0 13 14 1 0 0 0 0 14 7 1 6 0 0 0 15 24 1 0 0 0 0 16 17 2 0 0 0 0 17 18 1 0 0 0 0 18 21 2 0 0 0 0 19 20 1 0 0 0 0 19 22 1 1 0 0 0 20 16 1 6 0 0 0 20 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	326.2
Volume:	346.642
LogP:	3.108
LogD:	3.049
LogS:	-3.335
# Rotatable Bonds:	4
TPSA:	45.59
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.935
Synthetic Accessibility Score:	4.374
Fsp3:	0.55
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.718
MDCK Permeability:	1.6165675333468243e-05
Pgp-inhibitor:	0.961
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.981
30% Bioavailability (F30%):	0.048

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.946
Plasma Protein Binding (PPB):	70.56800079345703%
Volume Distribution (VD):	2.39
Pgp-substrate:	20.861806869506836%

ADMET: Metabolism

CYP1A2-inhibitor:	0.26
CYP1A2-substrate:	0.946
CYP2C19-inhibitor:	0.34
CYP2C19-substrate:	0.923
CYP2C9-inhibitor:	0.077
CYP2C9-substrate:	0.588
CYP2D6-inhibitor:	0.963
CYP2D6-substrate:	0.924
CYP3A4-inhibitor:	0.337
CYP3A4-substrate:	0.683

ADMET: Excretion

Clearance (CL):	3.128
Half-life (T1/2):	0.307

ADMET: Toxicity

hERG Blockers:	0.786
Human Hepatotoxicity (H-HT):	0.95
Drug-inuced Liver Injury (DILI):	0.887
AMES Toxicity:	0.261
Rat Oral Acute Toxicity:	0.702
Maximum Recommended Daily Dose:	0.315
Skin Sensitization:	0.646
Carcinogencity:	0.393
Eye Corrosion:	0.003
Eye Irritation:	0.078
Respiratory Toxicity:	0.952

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC47059

Natural Product ID:	NPC47059
*Common Name:**	(R)-[(2S,4R,5S)-5-Ethyl-1-Azabicyclo[2.2.2]Octan-2-Yl]-(6-Methoxyquinolin-4-Yl)Methanol
IUPAC Name:	(R)-[(2S,4R,5S)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol
Synonyms:
Standard InCHIKey:	LJOQGZACKSYWCH-VPCNSNALSA-N
Standard InCHI:	InChI=1S/C20H26N2O2/c1-3-13-12-22-9-7-14(13)10-19(22)20(23)16-6-8-21-18-5-4-15(24-2)11-17(16)18/h4-6,8,11,13-14,19-20,23H,3,7,9-10,12H2,1-2H3/t13-,14-,19+,20-/m1/s1
SMILES:	CC[C@@H]1CN2CC[C@@H]1C[C@H]2[C@@H](c1ccnc2c1cc(OC)cc2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1436416
PubChem CID:	6916040
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0002246] Cinchona alkaloids

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO25089	Cinchona calisaya	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11992775]
NPO30377	Cinchona ledgeriana	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22736.1	Drosera peltata var. lunata	Varieties	Droseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22054	Cinchona officinalis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25089	Cinchona calisaya	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22736.1	Drosera peltata var. lunata	Varieties	Droseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22054	Cinchona officinalis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO30377	Cinchona ledgeriana	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22054	Cinchona officinalis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25089	Cinchona calisaya	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
Potency	11

Activity Type	# Activity
Individual Protein	8
Others	2
Protein-Protein Interaction	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT149	Individual Protein	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	Homo sapiens	Potency	=	25118.9	nM	PMID[570112]
NPT48	Individual Protein	Lysine-specific demethylase 4D-like	Homo sapiens	Potency	=	22387.2	nM	PMID[570112]
NPT151	Individual Protein	15-hydroxyprostaglandin dehydrogenase [NAD+]	Homo sapiens	Potency	=	39810.7	nM	PMID[570112]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	Potency	=	398.1	nM	PMID[570112]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	11885.6	nM	PMID[570112]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	6683.8	nM	PMID[570112]
NPT197	Protein-Protein Interaction	Menin/Histone-lysine N-methyltransferase MLL	Homo sapiens	Potency	=	39810.7	nM	PMID[570112]
NPT94	Individual Protein	Aldehyde dehydrogenase 1A1	Homo sapiens	Potency	=	39810.7	nM	PMID[570112]
NPT2	Others	Unspecified		Potency	n.a.	35481.3	nM	PMID[570112]
NPT2	Others	Unspecified		Potency	n.a.	31622.8	nM	PMID[570112]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC47059 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	453
0.1-0.2	2056
0.2-0.3	10930
0.3-0.4	7807
0.4-0.5	15108
0.5-0.6	4034
0.6-0.7	1993
0.7-0.8	306
0.8-0.85	1
0.85-0.9	3
0.9-0.95	0
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC329708
1.0	High Similarity	NPC118832
1.0	High Similarity	NPC264166
1.0	High Similarity	NPC274291
1.0	High Similarity	NPC165349
0.8808	High Similarity	NPC472111
0.8674	High Similarity	NPC203754
0.8674	High Similarity	NPC150048
0.82	Intermediate Similarity	NPC193238
0.8154	Intermediate Similarity	NPC251090
0.8144	Intermediate Similarity	NPC307963
0.8119	Intermediate Similarity	NPC469589
0.8081	Intermediate Similarity	NPC249040
0.805	Intermediate Similarity	NPC475774
0.8041	Intermediate Similarity	NPC92111
0.803	Intermediate Similarity	NPC4071
0.803	Intermediate Similarity	NPC476582
0.803	Intermediate Similarity	NPC476578
0.8009	Intermediate Similarity	NPC295228
0.8	Intermediate Similarity	NPC202605
0.8	Intermediate Similarity	NPC112206
0.799	Intermediate Similarity	NPC76748
0.797	Intermediate Similarity	NPC475841
0.797	Intermediate Similarity	NPC474145
0.7938	Intermediate Similarity	NPC296527
0.7921	Intermediate Similarity	NPC476581
0.7921	Intermediate Similarity	NPC36229
0.7921	Intermediate Similarity	NPC16452
0.7906	Intermediate Similarity	NPC219963
0.79	Intermediate Similarity	NPC329793
0.7895	Intermediate Similarity	NPC469594
0.7892	Intermediate Similarity	NPC477111
0.7874	Intermediate Similarity	NPC471080
0.7874	Intermediate Similarity	NPC469592
0.783	Intermediate Similarity	NPC280272
0.7826	Intermediate Similarity	NPC26679
0.7819	Intermediate Similarity	NPC252590
0.7817	Intermediate Similarity	NPC133140
0.7817	Intermediate Similarity	NPC195268
0.7816	Intermediate Similarity	NPC5145
0.7811	Intermediate Similarity	NPC315957
0.7811	Intermediate Similarity	NPC176538
0.7805	Intermediate Similarity	NPC82548
0.7799	Intermediate Similarity	NPC470799
0.7799	Intermediate Similarity	NPC8022
0.7799	Intermediate Similarity	NPC477110
0.7789	Intermediate Similarity	NPC473053
0.7788	Intermediate Similarity	NPC469554
0.7788	Intermediate Similarity	NPC266931
0.7784	Intermediate Similarity	NPC177404
0.7778	Intermediate Similarity	NPC289786
0.7778	Intermediate Similarity	NPC226202
0.7772	Intermediate Similarity	NPC31930
0.7766	Intermediate Similarity	NPC473764
0.7766	Intermediate Similarity	NPC314940
0.7762	Intermediate Similarity	NPC476041
0.7762	Intermediate Similarity	NPC304926
0.7761	Intermediate Similarity	NPC287437
0.7756	Intermediate Similarity	NPC313189
0.775	Intermediate Similarity	NPC267928
0.775	Intermediate Similarity	NPC224928
0.7744	Intermediate Similarity	NPC171171
0.774	Intermediate Similarity	NPC472098
0.772	Intermediate Similarity	NPC161887
0.772	Intermediate Similarity	NPC266551
0.7718	Intermediate Similarity	NPC475910
0.7707	Intermediate Similarity	NPC477113
0.7706	Intermediate Similarity	NPC101543
0.7704	Intermediate Similarity	NPC66083
0.7692	Intermediate Similarity	NPC314002
0.7692	Intermediate Similarity	NPC208284
0.7689	Intermediate Similarity	NPC213530
0.7689	Intermediate Similarity	NPC193267
0.7688	Intermediate Similarity	NPC124542
0.7688	Intermediate Similarity	NPC471177
0.7688	Intermediate Similarity	NPC59779
0.7681	Intermediate Similarity	NPC185782
0.7671	Intermediate Similarity	NPC255800
0.7671	Intermediate Similarity	NPC96584
0.7661	Intermediate Similarity	NPC201508
0.7659	Intermediate Similarity	NPC470500
0.7659	Intermediate Similarity	NPC475070
0.7656	Intermediate Similarity	NPC296482
0.7656	Intermediate Similarity	NPC202768
0.7656	Intermediate Similarity	NPC53069
0.7653	Intermediate Similarity	NPC472099
0.765	Intermediate Similarity	NPC26872
0.7647	Intermediate Similarity	NPC118511
0.7644	Intermediate Similarity	NPC312872
0.7644	Intermediate Similarity	NPC290689
0.7642	Intermediate Similarity	NPC173080
0.7641	Intermediate Similarity	NPC204717
0.7638	Intermediate Similarity	NPC99666
0.7635	Intermediate Similarity	NPC234197
0.7623	Intermediate Similarity	NPC81175
0.7622	Intermediate Similarity	NPC26850
0.7621	Intermediate Similarity	NPC323345
0.7621	Intermediate Similarity	NPC470164
0.761	Intermediate Similarity	NPC245816
0.761	Intermediate Similarity	NPC476138
0.7606	Intermediate Similarity	NPC471178
0.759	Intermediate Similarity	NPC220765
0.7585	Intermediate Similarity	NPC135549
0.7581	Intermediate Similarity	NPC122463
0.7573	Intermediate Similarity	NPC285558
0.7571	Intermediate Similarity	NPC316981
0.757	Intermediate Similarity	NPC174049
0.7569	Intermediate Similarity	NPC314954
0.7565	Intermediate Similarity	NPC326575
0.7565	Intermediate Similarity	NPC283152
0.7551	Intermediate Similarity	NPC62069
0.7549	Intermediate Similarity	NPC477019
0.7549	Intermediate Similarity	NPC19872
0.7548	Intermediate Similarity	NPC287208
0.7545	Intermediate Similarity	NPC475720
0.7545	Intermediate Similarity	NPC474192
0.7539	Intermediate Similarity	NPC121658
0.7539	Intermediate Similarity	NPC14651
0.7538	Intermediate Similarity	NPC3715
0.7536	Intermediate Similarity	NPC478074
0.7535	Intermediate Similarity	NPC310118
0.7524	Intermediate Similarity	NPC223427
0.7523	Intermediate Similarity	NPC110151
0.7513	Intermediate Similarity	NPC472122
0.7513	Intermediate Similarity	NPC24594
0.7513	Intermediate Similarity	NPC42591
0.7512	Intermediate Similarity	NPC279401
0.7512	Intermediate Similarity	NPC79293
0.75	Intermediate Similarity	NPC176127
0.7488	Intermediate Similarity	NPC96405
0.7488	Intermediate Similarity	NPC132642
0.7488	Intermediate Similarity	NPC171409
0.7487	Intermediate Similarity	NPC187827
0.7487	Intermediate Similarity	NPC476518
0.7487	Intermediate Similarity	NPC472105
0.7477	Intermediate Similarity	NPC473822
0.7476	Intermediate Similarity	NPC123976
0.7476	Intermediate Similarity	NPC471304
0.7476	Intermediate Similarity	NPC211813
0.7476	Intermediate Similarity	NPC167860
0.7465	Intermediate Similarity	NPC288349
0.7464	Intermediate Similarity	NPC476465
0.7449	Intermediate Similarity	NPC470474
0.7445	Intermediate Similarity	NPC472434
0.7443	Intermediate Similarity	NPC6215
0.7436	Intermediate Similarity	NPC133261
0.7426	Intermediate Similarity	NPC329541
0.7424	Intermediate Similarity	NPC62510
0.7416	Intermediate Similarity	NPC53344
0.7413	Intermediate Similarity	NPC469390
0.7406	Intermediate Similarity	NPC264176
0.7404	Intermediate Similarity	NPC164374
0.7404	Intermediate Similarity	NPC137929
0.7402	Intermediate Similarity	NPC77555
0.74	Intermediate Similarity	NPC32771
0.7397	Intermediate Similarity	NPC103687
0.7397	Intermediate Similarity	NPC132631
0.7395	Intermediate Similarity	NPC204446
0.7394	Intermediate Similarity	NPC84508
0.7393	Intermediate Similarity	NPC11464
0.7393	Intermediate Similarity	NPC470020
0.7391	Intermediate Similarity	NPC470678
0.7389	Intermediate Similarity	NPC99891
0.7385	Intermediate Similarity	NPC184964
0.7371	Intermediate Similarity	NPC149471
0.7371	Intermediate Similarity	NPC162530
0.7371	Intermediate Similarity	NPC271215
0.7349	Intermediate Similarity	NPC473513
0.7346	Intermediate Similarity	NPC174672
0.7346	Intermediate Similarity	NPC476116
0.7346	Intermediate Similarity	NPC174758
0.7345	Intermediate Similarity	NPC475816
0.7343	Intermediate Similarity	NPC232727
0.7339	Intermediate Similarity	NPC216612
0.7337	Intermediate Similarity	NPC20249
0.7333	Intermediate Similarity	NPC288943
0.7333	Intermediate Similarity	NPC134586
0.733	Intermediate Similarity	NPC476167
0.7324	Intermediate Similarity	NPC251160
0.7323	Intermediate Similarity	NPC472110
0.7323	Intermediate Similarity	NPC472109
0.732	Intermediate Similarity	NPC111624
0.7318	Intermediate Similarity	NPC214980
0.7317	Intermediate Similarity	NPC156704
0.7311	Intermediate Similarity	NPC188420
0.731	Intermediate Similarity	NPC222592
0.731	Intermediate Similarity	NPC168486
0.73	Intermediate Similarity	NPC204385
0.7296	Intermediate Similarity	NPC211997
0.7295	Intermediate Similarity	NPC329747
0.7295	Intermediate Similarity	NPC315491
0.7295	Intermediate Similarity	NPC45459
0.729	Intermediate Similarity	NPC476287
0.7289	Intermediate Similarity	NPC477549
0.7286	Intermediate Similarity	NPC284559
0.7284	Intermediate Similarity	NPC137353
0.7282	Intermediate Similarity	NPC192315
0.7282	Intermediate Similarity	NPC239954
0.7277	Intermediate Similarity	NPC473105
0.7273	Intermediate Similarity	NPC469440

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC47059 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	244
0.1-0.2	605
0.2-0.3	867
0.3-0.4	1345
0.4-0.5	2598
0.5-0.6	2358
0.6-0.7	932
0.7-0.8	187
0.8-0.85	4
0.85-0.9	1
0.9-0.95	3
0.95-1	6

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD31	Approved
1.0	High Similarity	NPD4034	Approved
1.0	High Similarity	NPD4037	Approved
1.0	High Similarity	NPD4122	Approved
1.0	High Similarity	NPD4039	Approved
1.0	High Similarity	NPD4038	Approved
1.0	High Similarity	NPD4035	Approved
1.0	High Similarity	NPD32	Approved
1.0	High Similarity	NPD4033	Approved
1.0	High Similarity	NPD4036	Approved
0.8632	High Similarity	NPD3478	Clinical (unspecified phase)
0.8632	High Similarity	NPD3477	Phase 2
0.8474	Intermediate Similarity	NPD6569	Phase 2
0.8201	Intermediate Similarity	NPD5083	Clinical (unspecified phase)
0.82	Intermediate Similarity	NPD7222	Phase 2
0.8144	Intermediate Similarity	NPD1038	Approved
0.8098	Intermediate Similarity	NPD6872	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD7414	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD4203	Approved
0.8	Intermediate Similarity	NPD1856	Discontinued
0.8	Intermediate Similarity	NPD4204	Approved
0.7959	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7951	Intermediate Similarity	NPD4502	Phase 2
0.7931	Intermediate Similarity	NPD7453	Approved
0.7931	Intermediate Similarity	NPD7452	Approved
0.7927	Intermediate Similarity	NPD4375	Approved
0.7921	Intermediate Similarity	NPD4795	Phase 2
0.7917	Intermediate Similarity	NPD6494	Phase 2
0.7885	Intermediate Similarity	NPD5612	Discontinued
0.7869	Intermediate Similarity	NPD5255	Approved
0.7868	Intermediate Similarity	NPD6361	Phase 2
0.7868	Intermediate Similarity	NPD4551	Phase 2
0.7848	Intermediate Similarity	NPD6276	Discontinued
0.7847	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7828	Intermediate Similarity	NPD6861	Clinical (unspecified phase)
0.7817	Intermediate Similarity	NPD3922	Approved
0.7817	Intermediate Similarity	NPD3921	Approved
0.7817	Intermediate Similarity	NPD3924	Approved
0.7817	Intermediate Similarity	NPD3923	Approved
0.7812	Intermediate Similarity	NPD3386	Phase 2
0.7811	Intermediate Similarity	NPD4396	Clinical (unspecified phase)
0.7811	Intermediate Similarity	NPD1739	Approved
0.7811	Intermediate Similarity	NPD1740	Approved
0.7804	Intermediate Similarity	NPD7675	Phase 3
0.7804	Intermediate Similarity	NPD7676	Clinical (unspecified phase)
0.7804	Intermediate Similarity	NPD7674	Phase 3
0.7773	Intermediate Similarity	NPD3402	Phase 1
0.7772	Intermediate Similarity	NPD5522	Clinical (unspecified phase)
0.7761	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7749	Intermediate Similarity	NPD1032	Phase 2
0.7725	Intermediate Similarity	NPD6568	Discontinued
0.7721	Intermediate Similarity	NPD7426	Phase 1
0.7716	Intermediate Similarity	NPD8063	Discontinued
0.7714	Intermediate Similarity	NPD7112	Discontinued
0.7708	Intermediate Similarity	NPD1620	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD5530	Phase 1
0.7704	Intermediate Similarity	NPD1033	Clinical (unspecified phase)
0.7704	Intermediate Similarity	NPD1034	Phase 3
0.7704	Intermediate Similarity	NPD6257	Clinical (unspecified phase)
0.77	Intermediate Similarity	NPD6550	Discontinued
0.7692	Intermediate Similarity	NPD4889	Approved
0.7689	Intermediate Similarity	NPD6500	Approved
0.7689	Intermediate Similarity	NPD6501	Approved
0.7688	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD2177	Approved
0.7673	Intermediate Similarity	NPD2175	Phase 3
0.7673	Intermediate Similarity	NPD5999	Phase 2
0.7673	Intermediate Similarity	NPD2176	Approved
0.7671	Intermediate Similarity	NPD7558	Phase 2
0.7667	Intermediate Similarity	NPD6140	Clinical (unspecified phase)
0.7656	Intermediate Similarity	NPD6159	Phase 2
0.7656	Intermediate Similarity	NPD7069	Discontinued
0.7656	Intermediate Similarity	NPD3815	Phase 1
0.7656	Intermediate Similarity	NPD3816	Phase 1
0.765	Intermediate Similarity	NPD6590	Discontinued
0.7634	Intermediate Similarity	NPD9705	Discontinued
0.7634	Intermediate Similarity	NPD112	Approved
0.7626	Intermediate Similarity	NPD4081	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD2582	Approved
0.7622	Intermediate Similarity	NPD2581	Approved
0.7608	Intermediate Similarity	NPD5067	Phase 2
0.7608	Intermediate Similarity	NPD5066	Phase 2
0.7604	Intermediate Similarity	NPD6553	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD3825	Phase 3
0.7585	Intermediate Similarity	NPD1392	Approved
0.7576	Intermediate Similarity	NPD4021	Phase 2
0.7574	Intermediate Similarity	NPD2952	Discontinued
0.7562	Intermediate Similarity	NPD3395	Approved
0.7562	Intermediate Similarity	NPD3396	Approved
0.7552	Intermediate Similarity	NPD9690	Approved
0.7547	Intermediate Similarity	NPD6147	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD7797	Approved
0.7545	Intermediate Similarity	NPD7796	Approved
0.7538	Intermediate Similarity	NPD6281	Approved
0.7536	Intermediate Similarity	NPD5945	Phase 1
0.7536	Intermediate Similarity	NPD5944	Phase 1
0.7525	Intermediate Similarity	NPD2383	Phase 1
0.7524	Intermediate Similarity	NPD6991	Approved
0.7513	Intermediate Similarity	NPD2381	Approved
0.7513	Intermediate Similarity	NPD2380	Approved
0.7513	Intermediate Similarity	NPD2382	Approved
0.7513	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7512	Intermediate Similarity	NPD4437	Phase 3
0.7512	Intermediate Similarity	NPD9695	Approved
0.7489	Intermediate Similarity	NPD5559	Phase 2
0.7478	Intermediate Similarity	NPD7859	Phase 2
0.7477	Intermediate Similarity	NPD3354	Phase 2
0.7476	Intermediate Similarity	NPD6477	Clinical (unspecified phase)
0.7476	Intermediate Similarity	NPD5669	Clinical (unspecified phase)
0.7475	Intermediate Similarity	NPD4919	Phase 3
0.7475	Intermediate Similarity	NPD4418	Discontinued
0.7475	Intermediate Similarity	NPD4921	Phase 3
0.7475	Intermediate Similarity	NPD4920	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD8101	Phase 3
0.7464	Intermediate Similarity	NPD2187	Approved
0.7464	Intermediate Similarity	NPD2189	Approved
0.7455	Intermediate Similarity	NPD7729	Clinical (unspecified phase)
0.7454	Intermediate Similarity	NPD5147	Discontinued
0.7453	Intermediate Similarity	NPD1322	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD7889	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD1078	Clinical (unspecified phase)
0.7441	Intermediate Similarity	NPD6220	Phase 3
0.7438	Intermediate Similarity	NPD5512	Phase 3
0.7435	Intermediate Similarity	NPD5862	Discovery
0.7433	Intermediate Similarity	NPD4671	Clinical (unspecified phase)
0.7433	Intermediate Similarity	NPD4669	Clinical (unspecified phase)
0.7433	Intermediate Similarity	NPD4670	Clinical (unspecified phase)
0.743	Intermediate Similarity	NPD4989	Phase 2
0.7418	Intermediate Similarity	NPD7538	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD5429	Discontinued
0.7407	Intermediate Similarity	NPD6242	Discontinued
0.7405	Intermediate Similarity	NPD6158	Phase 2
0.7405	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7402	Intermediate Similarity	NPD6769	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD5640	Discontinued
0.7395	Intermediate Similarity	NPD8109	Clinical (unspecified phase)
0.7395	Intermediate Similarity	NPD4429	Discontinued
0.7391	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD6491	Clinical (unspecified phase)
0.7387	Intermediate Similarity	NPD3039	Clinical (unspecified phase)
0.7385	Intermediate Similarity	NPD5751	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD5658	Approved
0.7381	Intermediate Similarity	NPD2739	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD7671	Approved
0.7381	Intermediate Similarity	NPD7672	Approved
0.7381	Intermediate Similarity	NPD5528	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD5529	Phase 1
0.7381	Intermediate Similarity	NPD5863	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD4372	Phase 1
0.7376	Intermediate Similarity	NPD7567	Approved
0.7376	Intermediate Similarity	NPD5022	Discontinued
0.7371	Intermediate Similarity	NPD1923	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD3003	Approved
0.7358	Intermediate Similarity	NPD5936	Approved
0.7358	Intermediate Similarity	NPD5939	Approved
0.7358	Intermediate Similarity	NPD3570	Phase 2
0.7358	Intermediate Similarity	NPD4131	Phase 3
0.7347	Intermediate Similarity	NPD3920	Phase 2
0.7344	Intermediate Similarity	NPD2781	Approved
0.7336	Intermediate Similarity	NPD8100	Phase 3
0.7333	Intermediate Similarity	NPD6290	Phase 2
0.7333	Intermediate Similarity	NPD4344	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD4343	Phase 1
0.733	Intermediate Similarity	NPD2782	Approved
0.733	Intermediate Similarity	NPD2780	Approved
0.733	Intermediate Similarity	NPD925	Approved
0.733	Intermediate Similarity	NPD926	Approved
0.733	Intermediate Similarity	NPD7555	Discontinued
0.733	Intermediate Similarity	NPD4548	Discontinued
0.7327	Intermediate Similarity	NPD4148	Approved
0.7327	Intermediate Similarity	NPD2334	Discontinued
0.7324	Intermediate Similarity	NPD3330	Phase 1
0.7317	Intermediate Similarity	NPD7948	Phase 1
0.7317	Intermediate Similarity	NPD1622	Discontinued
0.7304	Intermediate Similarity	NPD3810	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD6803	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD7589	Clinical (unspecified phase)
0.7295	Intermediate Similarity	NPD484	Approved
0.7295	Intermediate Similarity	NPD6219	Discontinued
0.7289	Intermediate Similarity	NPD3006	Discontinued
0.7282	Intermediate Similarity	NPD5065	Approved
0.7277	Intermediate Similarity	NPD7169	Suspended
0.726	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD4897	Phase 2
0.7255	Intermediate Similarity	NPD4526	Approved
0.7255	Intermediate Similarity	NPD4529	Approved
0.7255	Intermediate Similarity	NPD4528	Approved
0.725	Intermediate Similarity	NPD7424	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD5930	Phase 3
0.7246	Intermediate Similarity	NPD1768	Approved
0.7244	Intermediate Similarity	NPD6963	Approved
0.7244	Intermediate Similarity	NPD6964	Approved
0.7235	Intermediate Similarity	NPD7395	Discontinued
0.7233	Intermediate Similarity	NPD6988	Phase 1
0.7231	Intermediate Similarity	NPD2077	Approved
0.7231	Intermediate Similarity	NPD2076	Approved
0.7225	Intermediate Similarity	NPD6750	Phase 2
0.7225	Intermediate Similarity	NPD6975	Discontinued
0.7225	Intermediate Similarity	NPD3931	Approved
0.7225	Intermediate Similarity	NPD3928	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data